Diisopropylamine → HCID 178491369, compound

HRID 447935Notes

Reaction equation

[Br-].[CH3:2][O:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([O:18]CC)=O)[N:15]=1)=[NH:9].[CH:27]([NH:30]C(C)C)([CH3:29])[CH3:28]>ClCCl>[CH3:26][O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:4]([O:3][CH3:2])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:30][CH:27]([CH3:29])[CH3:28])=[O:18])[N:15]=1)=[NH:9]

Participants

Conditions

Temperature: 60 °C

Procedure

0.157 g (0.35 mmol) ethyl 2-{[[(2,6-dimethoxybenzyl)amino](imino)methyl]amino}-1,3-thiazole-4-carboxylate bromide were combined with 1.50 ml (17.28 mmol) diisopropylamine and were heated in the microwave at 50 to 70° C. (150 Watt) for 2 hours. In this example, complete reaction was achieved only after further heating in the microwave at 70° C. (150 Watt) by “heating by cooling” after 4.5 hours. The reaction mixture was diluted with 20 ml dichlormethane and was washed with water (3×30 ml). After drying over MgSO4, filtration and removal of the organic solvent under vacuum, the mixture was purified on preparative HPLC (Merck: Chromolith RP-18E, 100-25; eluent water/acetonitrile/0.1 molar acetic acid). 26 mg of 2-{[[(2,6-dimethoxybenzyl)amino](imino)methyl]amino}-N-isopropyl-1,3-thiazole-4-carboxamide were isolated.

Workup

temperatureafter further heating in the microwave at 70° C. (150 Watt) by “
temperatureheating
temperatureby cooling” after 4.5 hours
washwas washed with water (3×30 ml)
dry with materialAfter drying over MgSO4, filtration and removal of the organic solvent under vacuum
customthe mixture was purified on preparative HPLC (Merck: Chromolith RP-18E, 100-25; eluent water/acetonitrile/0.1 molar acetic acid)

Sources & evidence

ORD record: ord-b7856f4dd0744312a9c5565ed9dc1b8f
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481576B2

Reaction notes

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